On Representation


I never thought much  about growing up in a place where black people played tennis. It just happened that my hometown happened to have the best public tennis facility in our area, so much that people from suburban areas would flock to our courts to play and practice with coaches our in town.

I think a lot about this, because I realized when I was in my late 20s that growing up where I did probably shaped much of my worldview in ways that being someplace else might not have. I’m not saying it was all perfect, it was far from that. But just the access to influences who didn’t just look like me, but who were a melange of characters who demanded excellence in different ways, helped shape my perspective because I wasn’t a stranger to black excellence. Not only that, it never occurred to me that there were jobs or things off-limits to me because growing up I saw black people who did everything. My first doctor was black, all of my school principals except one were black — my first elementary school principal was a black woman for 5 of the 6 years I was in that school.

Even the white teachers I had seemed to be hellbent on teaching us in ways that defied conventional expectations. We were reading Orwell in elementary school. We participated in activities like Odyssey of The Mind that took us away from our town and around the state and region to compete — and succeed at high levels.  When I lived  in distant places years later, it occurred to me at different times there were people who simply had never encountered a black person in a leadership position. Or a black dude who was the tech guy and not the basketball coach. I joke about this sometimes, but it really does matter. How people see  you doesn’t just affect how they treat you, it impacts the range of opportunities you’re offered and the ways people perceive your smarts because  they’re not quite sure how you got where you are — since they’ve never seen anyone doing what you’re doing.

That’s not my problem, though. And yet, it becomes my problem more often than now. It doesn’t excuse being less than excellent. Make no mistake, I’ve been afforded some fantastic mentors and people throughout my adult life who have seen things in me I had not yet seen in myself. They’ve supported my goals, encouraged me and tried to connect me to bigger and better things. Almost none of them looked anything like the people I grew up with.

I just felt the need to connect the dots on representation. I know some people look at “firsts” in 2016 and think even the mention of such things is a step backwards. “Why does it matter?” “Why can’t we just celebrate these accomplishments as Americans?” We can, but there’s an added joy to defying expectations, especially when there are structural barriers to many of the things that people still want to do today. Remember that successful might happen globally or nationally, but it starts locally.

Think of bridge trolls as gatekeepers. Every time you want to do something, there might be one person to determine whether you get to do it or not. Sure, you can go to another town but that takes time and money. Or find a private club that’ll accept you. Maybe it’s just finding someone who sees your ability and talent and is willing to nurture it. Success is measured in small distances, not big gaps, especially at the elite level. What separates the people who make it, is often a matter of timing and opportunity.

Whenever there’s some historic achievement where someone is mentioned to be the “first” to do something — specifically here in America — I often vacillate between being annoyed that we have to mention it and grateful that we live in a time where such barriers are falling.

I try to reflect on every moment  as if it’s penance to the people who  were denied access, who fought and broke rules and raised hell to give their forebears access to the opportunities they now enjoy freely.

Every time you hear “so and so is the first _____ to do _____,” it’s a little whisper of apology from every single person who might not have been complicit, but part of the collective debt we all share from a past with fingerprints all over our lives today and how we live them.

Designing a better city

On design & policy. Have you ever noticed how small the print is on subway ticket purchasing machines? How often do you think about the hundreds of touchpoints throughout your day that comprise whether you go home feeling like you had a good day or not? Every part of the experience of your interaction with the communities where we live and work are design decisions made by someone faceless. The choice could have been the result of a series of meetings 95 years ago or a change made last week. We rarely know the difference.

I’ve been thinking a lot about the intersection of tech, marketing and just digital strategy as a whole. People like me spend a lot of time in offices and within entities using brainpower to ultimately figure out how to sell more widgets. Maybe those widgets are enrolling more college students or selling more sneakers or helping a brand humanize itself to stakeholders. 

Along the way, I’ve spent a lot of time pondering ways to be a broader contributor to real problems that we face in communities across the country, but wasn’t precisely sure how to fuse together the design and tech parts with policy.

Being new to a city is a special kind of hell. Unless you already have familiarity with the place you’re moving to or have some other connection (work, relationship or family) that can bridge you from ‘stranger’ to ‘part of the tribe’ it can take years to on-board your way through the morass of written and unwritten ways that our communities are designed to thwart outsiders. Not all of this deliberate, but these challenges have real impacts.

Every place is different. For every community that’s hostile to outsiders, there are others desperate for an injection of interest from afar.

With the increasing number of quasi-governmental projects springing up that want to figure out how to bring tech innovation to government, I’ve been contemplating how to use design as a tool to expand our vocabulary and imagination about the future of our communities.

Here’s the thing, I’m not as interested in whether we can create tech solutions to structural problems. If building a better website or doing user research to solve a community problem like access to summer meals for kids or helping making paying utility bills more efficient, then I’m all for figuring out the ways that tech can help us.

What if we could use the tools, frameworks and vocabulary of design to inform policy? Ideas are important, but only when they lead to impact. We need entities that help policymakers, stakeholders and citizens work together, engage and collaborate to solve problems. 

Strategic Design is a discipline that comes to us from Finland and it’s mostly concerned with solving big structural problems that cities, governments and organizations face. 

“Strategic design has a set of direction, over and above being a set of tools, a vocabulary and a series of projects. Its focus is in enabling systemic change through re-shaped cultures of public decision-making at the individual and institutional levels, applied to the primary problems of 21st century governance.” — Dan Hill, Dark Matter and Trojan Horses

While we already have wonderful folks at places like Code for America, 18F and the US Digital Service, what I’m talking about is far broader than tech conversations. Lately, the folks at Y Combinator have decided they want to tackle these issues too. 

I am sincere in my belief that the frameworks and vocabulary of strategic design can help advance our communities forward, by helping us think broadly about how we create barriers to progress for ordinary citizens everyday. 

Here’s how we move forward: Assembling an interdisciplinary group of doers. I’m calling this thing Design of the City. Designers, strategists and people in-between are welcome on this journey. I imagine at first there will be a few of us, but once we figure out what we’re doing, we’ll expand rapidly.
Engage with governments, non-governmental organizations, civic groups and even companies to view high-level challenges and use design tactics and processes to consider the aspects of these problems and develop solutions.
By engaging with an outside group of stakeholders who become embedded within the entity for a set period of time, we’re able to move quicker to begin diagnosing the challenges with traction. I don’t think this prevents the barriers that impede in-house solutions, but the fresh sets of eyes can be vital. 

I believe there are people who want to do more than just build products, we want to construct communities, services & structures that serve populations for the next hundred years. Much like the physical infrastructure of many cities, we have a policy and governance framework bequeathed to us from forebears that could not have imagine the distances we’d travel. We need to reflect and imagine a new set of rules, frameworks and invoke an imagination that allows to envision communities as vibrant and flexible. 

Incoherent thoughts on exploration


I’ve always been an explorer.

In a world where it’s often a lot easier to join something prefabricated, I’ve consistently taken the harder road towards building something of my own. One summer between my 7th and 8th grade year, I got the bright idea to start a baseball league. Not a team, an entire league.

As you can imagine, I had no idea clue about things like insurance, sponsors or even players. I called the local newspaper and for some reason, they printed my ad for players and for weeks, people from all over Central Jersey started calling my parents house about this baseball league. Whenever someone proposed a new challenge, I’d explore ways to solve it. From . insurance to sponsors, I talked my way into partnerships and alliances from grown adults who did not question my moxie.

As all good things do, the experiment only lasted a few weeks. I didn’t have enough players because who in their right mind lets a thirteen year old organize a baseball league with a straight face? But it was an interesting few weeks nonetheless.

That was only the first experiment.

With this path comes all of the inevitable challenges of trying to make a way out of nothing. What’s more difficult is getting to the point of realizing there’s only so much you can do by yourself. I don’t realize at the time how difficult the road is.

Whether it’s a conference or a shoe brand (both things I’ve done) or thinking about my own work trajectory and the future, I spend a lot of time contemplating what the so-called right way is. I’ve met enough smart people in my life, with life paths I’ve admired to know that there is no prototype to the canvas we paint on. We just start working and fill in the gaps as we go. Sometimes, you start over entirely. Except, there’s no such thing as truly starting from scratch.

It’s so alluring at a certain point to believe that you have to put on the armor of being a know-it-all, because we reward it. At least in America, anyway. You sit in meetings and these days, turn on the TV and watch people talk outside the side of their mouths with the faintest regard for whether anything they are saying really meshes with reality.

It’s frustrating to think that’s the way you’re supposed to get ahead. I’ve always favored a path, especially in recent years, of an earnest recognition of what I do not knowEmbracing the fuzziness makes me feel like I’ll get closer to answers I didn’t imagine, because I concede the things I’d like to learn more about. Probably not a winning strategy for proving you’re the smartest person there ever was, but that’s never been something I’ve wanted anyway.

So much of the challenge of knowing where you fit is assembling the right puzzle pieces for a life that makes you want to get up everyday poised to add more pieces. At least, that’s the formula in my head. As I get older, I keep feeling like it’s supposed to make more sense and the opposite ends up being true.

Much like playing an easy board game, you know where all of the pieces go and how they’re supposed to work. I just find that winning is harder and harder even as I’m better prepared than ever to play.

Perhaps it’s just being sure of the game you’re playing in the first place?

Show Your Work

You probably have a job like I did. Maybe you’re even an intern. Whatever. Anyway, you have some job and you’re doing whatever they’re asking of you. Some days, that’s writing some stuff. Other days, maybe it’s design and code. Regardless, you’re always doing something.

Here’s the problem. When you work at the intersection of tech and you’re doing work that nobody else around you understands, it becomes necessary to develop a shorthand for communicating with laymen.

At the risk of burying the lede, you need to start showing your work. Document what you’re doing, because nobody will ever tell you to do it at work. It’s easy to get really good at your job by simply knowing what you know, melding your processes with whatever your organization requires. It’s tempting when you’re a lone ranger to eschew with formal processes, because “people aren’t going to it anyway.”

The reason is easy. It’s the reason people laugh watching The IT Crowd or the stereotype of the cranky, know-it-all tech person exists. Having started my career as an IT guy, I knew the trope well. When I switched to the web, I was adamant about making the work accessible to people. Frankly, this applies whether your job is making artisanal french fries or doing UX. Most jobs have a language, but unlike working on your car or the plumbing getting stuck, there’s not a real need to engage in the language of the web everyday. It’s not until something breaks or needs to be fixed, that you need to start understanding what your “web person” is talking about.

Most of the people reading this on Medium somewhere probably don’t identify with this. If you’ve got some great job at some bleeding-edge startup in some semi-hip city off the continental shelf, you’re not dealing with the things ordinary people do everyday. The ones who are too busy to tweet; with bosses skeptical of social media and wondering why everything on the web takes so long to actually make.

Everyone has some kind of process. Documenting what you’re doing, even if it’s just for you, is a good way to signpost throughout your process. If you’re about to embark on an effort you’ve never performed before — a web redesign, user research, content audit — take the time to do some research about what other people have done before you get started. Do a search for other people’s frameworks, adapt them and move on. It’s tempting when you’re a lone wolf in an organization to feel like you need to know everything. There’s no one around to tell you otherwise. In fact, it probably feels like people actually do expect you to know everything because in their minds “that’s what we hired you for.”

Part of being a subject matter expert is understanding how to learn. Having a documented process, more than anything, gives you a chance to look back years later at what you did and helps you improve your methods. It took me years to realize how critical it was to document mental models and other tools that I used consistently on projects both large and small throughout my career thus far. I have some tools I used a lot, but the process of actually keeping track of my own progress came fairly late for me.

You can start today.